Highly active catalyst for the heterogeneous Suzuki-Miyaura reaction: assembled complex of palladium and non-cross-linked amphiphilic polymer

Yoichi M A Yamada; Koji Takeda; Hideyo Takahashi; Shiro Ikegami

doi:10.1021/jo034354v

Highly active catalyst for the heterogeneous Suzuki-Miyaura reaction: assembled complex of palladium and non-cross-linked amphiphilic polymer

J Org Chem. 2003 Oct 3;68(20):7733-41. doi: 10.1021/jo034354v.

Authors

Yoichi M A Yamada¹, Koji Takeda, Hideyo Takahashi, Shiro Ikegami

Affiliation

¹ Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-0195, Japan.

PMID: 14510549
DOI: 10.1021/jo034354v

Abstract

An assembled insoluble catalyst, PdAS, prepared from palladium ((NH4)2PdCl4 (1)) and non-cross-linked amphiphilic copolymer poly(N-isopropylacrylamide-co-4-diphenylstyrylphosphine) (2) was developed. It was found that PdAS is an excellent catalyst for the Suzuki-Miyaura reaction on three points: (1) The use of 8 x 10(-7) to 5 x 10(-4) mol equiv of PdAS afforded the coupling products efficiently after easy workup, with the turnover number reaching up to 1,250,000. (2) The catalyst was reusable many times without loss of catalytic activity. (3) PdAS showed good stability in any reaction medium (i.e., water or aqueous or anhydrous organic solvents). Analytical study of PdAS indicates that the phosphines in 2 coordinate to palladium to form PdCl2(PPh2Ar)2 species.